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Yes, basement insulation needs a vapor barrier due to its susceptibility to moisture seeping in from the outside of the house. You should install a moisture barrier before you install insulation or purchase insulation that comes prebuilt with a moisture barrier to avoid water damage in your insulation and costly mold and water remediation expenses. 

If you plan on heating your garage, you must install a vapor barrier when drywalling the garage. A vapor barrier protects your garage from frost and mold that can occur through condensation. If your garage is unheated, you don't need to install a vapor barrier. The only exception is if you regularly crank the heat in your car before getting in it. In this case, you may still want to install a vapor barrier, as your car can heat your garage.

A plastic vapor barrier should completely cover your basement to prevent water from penetrating through the walls. This typically goes before installing insulation to prevent moisture from building up and becoming trapped on the inside of your insulation, where it can collect and lead to mold damage. Installing insulation after the vapor barrier allows for any moisture to exit the walls for better ventilation.

Yes, insulating ductwork in a crawl space is a worthwhile investment, especially if you live in a colder climate or run your air conditioning for most of the year. Uninsulated ducts can lose up to 30% of their heating and cooling efficiency, which can significantly impact your electricity bill. The project is a relatively small investment and typically only takes a few hours. It's a particularly simple add-on if you are already hiring someone to insulate the entire crawl space. An added benefit is that insulated ducts put off less hot or cold air, making them less attractive to pests.